Dimethylacetamide → HCID 71208810, compound

HRID 2280251Notes

Reaction equation

CN([C:4]([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[C:46]3[C:41](=[N:42][CH:43]=[N:44][C:45]=3[NH2:47])[N:40]([C@@H:48]3[CH2:52][CH2:51][NH:50][CH2:49]3)[N:39]=2)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C[CH2:54][N:55]([CH:59]([CH3:61])C)[CH:56]([CH3:58])C.[CH3:62][C:63](N(C)C)=[O:64]>>[NH2:47][C:45]1[N:44]=[CH:43][N:42]=[C:41]2[N:40]([C@@H:48]3[CH2:52][CH2:51][N:50]([C:63](=[O:64])/[CH:62]=[CH:61]/[CH2:59][N:55]([CH2:56][CH2:58][O:8][CH3:4])[CH3:54])[CH2:49]3)[N:39]=[C:38]([C:35]3[CH:34]=[CH:33][C:32]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:37][CH:36]=3)[C:46]=12

Participants

Reactant 4

HCID 31374Dimethylacetamide2×

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 71208757HCID 71208757, compound

Product 1

HCID 71208810HCID 71208810, compound

Conditions

Temperature: 25 °C

Procedure

The solution of compound 10 (200 mg, 1.1 mmol) and HATU (439 mg, 1.1 mmol) in 10 mL of DMA was stirred at 25° C. for 10 mins. Then it was added to the solution of compound A (400 mg, 1.1 mmol) and DIPEA (298 mg, 2.3 mmol) in 10 mL of DMA, and the mixture was stirred at 25° C. for 3 h. The reaction was monitored by LC-MS, and purified by prep-HPLC to give 76 mg of the title compound (1g). MS (ESI) m/e (M+1H)+: 528.3.

Workup

custompurified by prep-HPLC

Sources & evidence

ORD record: ord-af1c2e368ed54636810a12e49c31e2a1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09138436B2

Reaction notes

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